Process for preparing 2-aminoethyl esters of methacrylic acid

Abstract

A process for preparing 2-aminoethyl esters of methacrylic acid by the reaction of methacrylic acid with an aziridine compound in a reaction solvent consisting of water or an aqueous solvent.

What is claimed is: 
     
       1. A process for preparing 2-aminoethyl esters of methacrylic acid comprising reacting methacrylic acid and an aziridine compound in a reaction solvent medium selected from the group consisting of water and an aqueous solvent at a temperature in the range of from 10° to 100° C. 
     
     
       2. The process as defined in claim 1, wherein a proportion of water to a total weight of the reaction mixture is in the range from 5 to 90 weight percent. 
     
     
       3. The process as defined in claim 1, wherein the ratio of F M  /F A  is in the range from 1/2 to 20/1, F M  representing the total number of moles of the methacrylic acid introduced, and F A  representing the total number of moles of the aziridine compound introduced. 
     
     
       4. The process as defined in claim 1, wherein the reaction is carried out while maintaining the ratio of C M  /C A  at least at 1.5, wherein C M  represents a molar concentration of the methacrylic acid and C A  represents a molar concentration of the aziridine compound. 
     
     
       5. The process as defined in claim 4, further comprising the steps of: adding an inorganic acid to the reaction mixture; and   carrying out the reaction while keeping a ratio of A/B at least at 1.5,   wherein A is an equivalent of free methacrylic acid and B is an equivalent of base of the aziridine compound in the reaction mixture.   
     
     
       6. The process as defined in claim 1, wherein said aziridine compound is selected from at least one member of the group consisting of ethyleneimine, propyleneimine, hydroxyethyl ethyleneimine, cyanoethyl ethyleneimine, and aminoethyl ethyleneimine. 
     
     
       7. A process for preparing 2-aminoethyl esters of methacrylic acid comprising reacting methacrylic acid and an aziridine compound in a reaction solvent medium selected from the group consisting of water and an aqueous solvent at a temperature in the range of from 10° C. to 100° C., wherein a proportion of water to a total weight of the reaction mixture is in the range from 5 to 90 weight percent, and wherein the ratio of F M  /F A  is in the range from 1/2 to 20/1, F M  representing the total number of moles of the methacrylic acid introduced, and F A  representing the total number of moles of the aziridine compound introduced. 
     
     
       8. A process for preparing 2-aminoethyl esters of methacrylic acid comprising reacting methacrylic acid and an aziridine compound represented by the formula: ##STR2## wherein R 1  and R 2  are respectively selected from the groups consisting of H and an alkyl with 1-4 carbon atoms, and R 3  is selected from the group consisting of H, an alkyl with 1-6 carbon atoms, an aralkyl with 7-12 carbon atoms, a cyanoalkyl with 2-6 carbon atoms, a hydroxyalkyl with 1-6 carbon atoms, and an aminoalkyl with 1-6 carbon atoms, in a reaction solvent medium selected from the group consisting of water and an aqueous solvent, at a temperature in the range of from 10° to 100° C. 
     
     
       9. A process for preparing 2-aminoethyl esters of methacrylic acid comprising reacting methacrylic acid and an aziridine compound selected from at least one member of the group consisting of ethyleneimine, propyleneimine, hydroxyethyl ethyleneimine, cyanoethyl ethyleneimine, and aminoethyl ethyleneimine in a reaction solvent medium selected from the group consisting of water and an aqueous solvent at a temperature in the range of from 10° to 100° C.